4-羟基-2,3-二甲氧基-4-(3-苯基丙-1-炔基)环丁-2-烯-1-酮 | 113976-71-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-羟基-2,3-二甲氧基-4-(3-苯基丙-1-炔基)环丁-2-烯-1-酮
• 英文名称: 2,3-Dimethoxy-4-hydroxy-4-(3-phenyl-1-propynyl)-2-cyclobuten-1-one
• 英文别名: 2-Cyclobuten-1-one, 4-hydroxy-2,3-dimethoxy-4-(3-phenyl-1-propynyl)-；4-hydroxy-2,3-dimethoxy-4-(3-phenylprop-1-ynyl)cyclobut-2-en-1-one
• CAS: 113976-71-9
• 化学式: C₁₅H₁₄O₄
• 分子量: 258.274
• InChiKey: IPRBTISUFOEHAW-UHFFFAOYSA-N

物化性质

• 熔点：
  86-87 °C
• 沸点：
  507.7±50.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-羟基-2,3-二甲氧基-4-(3-苯基丙-1-炔基)环丁-2-烯-1-酮 以 乙腈 为溶剂， 以65%的产率得到2,3-二甲氧基-5-(苯基甲基)-2,5-环己二烯-1,4-二酮
  参考文献：
  名称：

  DNA Cleavage by 4-Alkynyl-3-methoxy-4-hydroxycyclobutenones

  摘要：

  4-Alkynyl-3-methoxy-4-hydroxycyclobutenones, a readily available class of compounds, cleave supercoiled DNA by a mechanism that appears to require at least some involvement of diradical intermediates formed in the ring expansion of the cyclobutenones.

  DOI：

  10.1021/jo00088a002
• 作为产物：
  描述：

  3-苯-1-丙炔 、 3,4-二甲氧基-3-环丁烯-1,2-二酮 在 正丁基锂 作用下， 生成 4-羟基-2,3-二甲氧基-4-(3-苯基丙-1-炔基)环丁-2-烯-1-酮
  参考文献：
  名称：

  Rearrangement of 4-alkynylcyclobutenones. A new synthesis of 1,4-benzoquinones

  摘要：

  DOI：

  10.1021/ja00185a030

文献信息

• Photolysis of 4-substituted-4-hydroxy-3-cyclobuten-1-ones: a new route to butenolides from 4-hydroxycyclobutenones
  作者：Steven T. Perri、Lafayette D. Foland、Harold W. Moore

  DOI：10.1016/0040-4039(88)85284-5

  日期：1988.1

  ring closure to provide butenolide products. This transformation is envisaged to involve a stereoselective disrotatory electrocyclic ring opening to the corresponding conjugated ketene in which the C4 hydroxyl group rotates inward towards the ketene moiety. Intramolecular trapping of the ketene moiety with the proximal hydroxyl group results in the corresponding butenolide products.

  4-取代-4-羟基-3-环丁烯-1-酮的光解经历环电开环，然后闭环以提供丁烯内酯产物。设想该转化涉及向相应的共轭烯酮的立体选择性旋转环开环，其中C 4羟基朝着烯酮部分向内旋转。用近端羟基将烯酮部分分子内捕获产生相应的丁烯内酯产物。
• Synthesis of 4-substituted-3-alkoxy-3-cyclobutene-1,2-diones
  作者：Michael W. Reed、Daniel J. Pollart、Steven T. Perri、Lafayette D. Foland、Harold W. Moore

  DOI：10.1021/jo00246a016

  日期：1988.5
• Annelation reactions of 4-alkynylcyclobutenones. Formation of methylenebenzofurans
  作者：Simon L. Xu、Meng Taing、Harold W. Moore

  DOI：10.1021/jo00021a026

  日期：1991.10

  Thermolysis of a number of 4-alkynyl-4-(propargyloxy)cyclobutenones is reported. These studies show a remarkable rearrangement to methylenebenzofurans accompanied by remote alkene formation. The mechanism and scope of the reactions are discussed.
• A potentially general regiospecific synthesis of substituted quinones from dimethyl squarate
  作者：Leah M. Gayo、Michael P. Winters、Harold W. Moore

  DOI：10.1021/jo00051a040

  日期：1992.12

  A potentially general regiospecific synthesis of benzo- and naphthoquinones is described. This method starts with dimethyl squarate (1), which is converted to the cyclobutenone ketal 3 upon sequential treatment with an organolithium reagent and then BF3 etherate or TFAA in THF/methanol. Treatment of these with a second lithium reagent followed by hydrolysis gives the cyclobutenones 5. Addition of an alkynyl-, alkenyl- or aryllithium agent to 5 followed by hydrolysis of the ketal linkage gives the corresponding 4-alkynyl- 4-alkenyl- or 4-aryl-4-hydroxycyclobutenones 7-9, and these readily rearrange to the respective quinones or hydroquinones upon thermolysis in refluxing benzene. In a similar fashion, 15 was employed as a reagent to prepare mono- and disubstituted hydroquinones and quinones.
• Synthesis of benzoquinones and annulated derivatives from conjugated ketenes
  作者：Steven T. Perri、Lafayette D. Foland、Owen H. W. Decker、Harold W. Moore

  DOI：10.1021/jo00365a044

  日期：1986.7